I could use some encouragement and validation. (Maybe discussion on pros and cons too.) I'm afraid people won't see me as pretty anymore because I'm fatter than I've ever been and I'm thinking about really masculinizing my look.

Letting go of pretty girl privileges is hard when you've already had a lot of people disrespect you in general. I have issues with being passive, so people who hate themselves love to self project on me. People who pick apart women might pick me apart for showing off my manly side. And for being fat while at it.

Being a pretty boy is the vibe I like to have when manlier, I think I like the safety of checking off some "pretty people" boxes that go with societal expectations advertised in magazines. When in reality feeling good about how you look is more about the attitude of feeling cute than how close you look to what you see in magazines. I think I mostly dread not feeling cute because I'm afraid of how others might perceive me and put me down. Trying to seek social "safety" by looking as much like a magazine image as possible was how I felt the most insecure, and I'm doing it right now. Not at the level I used to, but I still am doing it.

For others seeking safety can mean passing on their own shame about their looks, and seeing a gender bender who's fat could either be freeing or lead to them choosing to double down and pass on their feelings of shame.